p-Toluenesulfonic acid monohydrate → HCID 67857874, compound

HRID 1586694Notes

Reaction equation

HRID 1586694 reaction equation
[CH3:1][C:2]([C:5]1[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[N:8]=[C:7]([CH:16](O)[CH:17]2[CH2:22][CH2:21][O:20][N:19]([CH3:23])[C:18]2=[O:24])[N:6]=1)([CH3:4])[CH3:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:4][C:2]([C:5]1[C:10]([OH:11])=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[N:8]=[C:7](/[CH:16]=[C:17]2/[C:18](=[O:24])[N:19]([CH3:23])[O:20][CH2:21][CH2:22]/2)[N:6]=1)([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 19759043HCID 19759043, compound

Product 1

HCID 67857874HCID 67857874, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 0.70 g (2.0 mmol) of 4-[[4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]hydroxymethyl]tetrahydro-2-methyl-2H-1,2-oxazin-3-one, Example 7, and 0.040 g (0.20 mmol) of p-toluenesulfonic acid monohydrate in 15 mL of toluene was stirred at reflux for 18 hours. The cooled reaction mixture was evaporated, and the residue was purified by flash chromatography (silica gel, 15% ethyl acetate in hexane elution) to yield 0.20 g (31%) of the title compound, mp 180°-181° C.; 1H NMR (deuteriochloroform) δ 1.46 (s, 18H), 3.36 (s, 3H), 3.46 (m, 2H), 4.21 (m, 2H), 5.25 (s, 1), 7.73 (s, 1H); MS m/e 334 (M+ +1).

Workup

  1. temperatureat reflux for 18 hours
  2. customThe cooled reaction mixture
  3. customwas evaporated
  4. customthe residue was purified by flash chromatography (silica gel, 15% ethyl acetate in hexane elution)

Sources & evidence

ORD record
ord-b5ba183808b745a3a1a0c2327182e705
Source dataset
uspto-grants-1993_06
Patent number
US05215986

Reaction notes

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